US8349832B2 - Compounds and compositions for treating cancer - Google Patents
Compounds and compositions for treating cancer Download PDFInfo
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- US8349832B2 US8349832B2 US12/874,306 US87430610A US8349832B2 US 8349832 B2 US8349832 B2 US 8349832B2 US 87430610 A US87430610 A US 87430610A US 8349832 B2 US8349832 B2 US 8349832B2
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- 0 *.CBCC.[1*]C.[2*]C.[3*]C Chemical compound *.CBCC.[1*]C.[2*]C.[3*]C 0.000 description 5
- VCAAKBGSSWALQC-RGWATLTBSA-K COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1C.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1O.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1OCCN1CCOCC1.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1OCCN1CCOCC1.Cl[Al](Cl)Cl.OCCN1CCOCC1 Chemical compound COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1C.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1O.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1OCCN1CCOCC1.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1OCCN1CCOCC1.Cl[Al](Cl)Cl.OCCN1CCOCC1 VCAAKBGSSWALQC-RGWATLTBSA-K 0.000 description 2
- BKLAWZQUIVDLMA-XLYMZMRCSA-K CC(C)(C)OC(=O)CCCO.CCCCOC1=C(C)C=C(/C=C/C(=O)OC)C=C1OC.CCO.CN(C)CCO.CN(CCO)C(=O)OC(C)(C)C.COC(=O)/C=C/C1=CC(C)=C(OCCN)C(OC)=C1.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1C.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1O.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1OCCCC(=O)OC(C)(C)C.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1OCCN(C)C(=O)OC(C)(C)C.ClCCN1CCOCC1.Cl[Al](Cl)Cl Chemical compound CC(C)(C)OC(=O)CCCO.CCCCOC1=C(C)C=C(/C=C/C(=O)OC)C=C1OC.CCO.CN(C)CCO.CN(CCO)C(=O)OC(C)(C)C.COC(=O)/C=C/C1=CC(C)=C(OCCN)C(OC)=C1.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1C.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1O.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1OCCCC(=O)OC(C)(C)C.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1OCCN(C)C(=O)OC(C)(C)C.ClCCN1CCOCC1.Cl[Al](Cl)Cl BKLAWZQUIVDLMA-XLYMZMRCSA-K 0.000 description 1
- RZFVPDSBVUNIQM-NTXIMEOBSA-K CC(C)(C)OC(=O)CCCO.CCO.CCOC1=C(C)C=C(/C=C/C(=O)N2CCC=CC2=O)C=C1OC.CN(C)CCO.CN(CCO)C(=O)OC(C)(C)C.CNCCOC1=C(C)C=C(/C=C/C(=O)N2CCC=CC2=O)C=C1OC.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1C.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1O.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1OCCN.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1OCCN(C)C.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1OCCN1CCOCC1.ClCCN1CCOCC1.Cl[Al](Cl)Cl Chemical compound CC(C)(C)OC(=O)CCCO.CCO.CCOC1=C(C)C=C(/C=C/C(=O)N2CCC=CC2=O)C=C1OC.CN(C)CCO.CN(CCO)C(=O)OC(C)(C)C.CNCCOC1=C(C)C=C(/C=C/C(=O)N2CCC=CC2=O)C=C1OC.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1C.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1O.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1OCCN.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1OCCN(C)C.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1OCCN1CCOCC1.ClCCN1CCOCC1.Cl[Al](Cl)Cl RZFVPDSBVUNIQM-NTXIMEOBSA-K 0.000 description 1
- BASRNDCJMUCSJU-LIGWRUNOSA-N CC(C)C1=CC=CC=C1.CC(C)C1=CC=C[Y]1.CC(C)C1=CC=[Y]C=C1.CC(C)C1=C[Y]=C[Y]=C1.CC(C)C1=[Y]C=[Y]C=C1 Chemical compound CC(C)C1=CC=CC=C1.CC(C)C1=CC=C[Y]1.CC(C)C1=CC=[Y]C=C1.CC(C)C1=C[Y]=C[Y]=C1.CC(C)C1=[Y]C=[Y]C=C1 BASRNDCJMUCSJU-LIGWRUNOSA-N 0.000 description 1
- SUFQMHBKUAJUKR-MSBQTRCSSA-N CCOC1=C(OC)C=C(/C=C/C(=O)N2CCC=CC2=O)C=C1C.CNCCOC1=C(OC)C=C(/C=C/C(=O)N2CCC=CC2=O)C=C1C.COC1=C(OCCN(C)C)C(C)=CC(/C=C/C(=O)N2CCC=CC2=O)=C1.COC1=C(OCCN)C(C)=CC(/C=C/C(=O)N2CCC=CC2=O)=C1.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1OCCN1CCOCC1 Chemical compound CCOC1=C(OC)C=C(/C=C/C(=O)N2CCC=CC2=O)C=C1C.CNCCOC1=C(OC)C=C(/C=C/C(=O)N2CCC=CC2=O)C=C1C.COC1=C(OCCN(C)C)C(C)=CC(/C=C/C(=O)N2CCC=CC2=O)=C1.COC1=C(OCCN)C(C)=CC(/C=C/C(=O)N2CCC=CC2=O)=C1.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1OCCN1CCOCC1 SUFQMHBKUAJUKR-MSBQTRCSSA-N 0.000 description 1
- XYQWNALYOXASOE-IVYONTGESA-N CNCCOC1=C(OC)C=C(/C=C/C(=O)N2CCC=CC2=O)C=C1C.COC1=C(OCCN(C)C)C(C)=CC(/C=C/C(=O)N2CCC=CC2=O)=C1.COC1=C(OCCN)C(C)=CC(/C=C/C(=O)N2CCC=CC2=O)=C1.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1OCCN1CCOCC1 Chemical compound CNCCOC1=C(OC)C=C(/C=C/C(=O)N2CCC=CC2=O)C=C1C.COC1=C(OCCN(C)C)C(C)=CC(/C=C/C(=O)N2CCC=CC2=O)=C1.COC1=C(OCCN)C(C)=CC(/C=C/C(=O)N2CCC=CC2=O)=C1.COC1=CC(/C=C/C(=O)N2CCC=CC2=O)=CC(C)=C1OCCN1CCOCC1 XYQWNALYOXASOE-IVYONTGESA-N 0.000 description 1
- BZJNPXPDHCHZHI-ONEGZZNKSA-N [H]C1C(=O)N(C(=O)/C=C/C2=CC(OC)=C(OCCN3CCOCC3)C(OC)=C2)CCC1Cl Chemical compound [H]C1C(=O)N(C(=O)/C=C/C2=CC(OC)=C(OCCN3CCOCC3)C(OC)=C2)CCC1Cl BZJNPXPDHCHZHI-ONEGZZNKSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
Definitions
- the present invention encompasses compounds having the following formula IA, or salts, derivatives, or mixtures thereof:
- FIG. 1 shows the effect of compounds on pancreatic cells
- compositions comprising the compounds have utility in the treatment of cancer.
Abstract
Description
- Ring A is selected from the group consisting of one or more monocyclic aryl, one or more heteroaryl, a 3-7 membered saturated or partially unsaturated carbocyclic ring, an 8-10 membered bicyclic saturated, partially unsaturated or aryl ring, a 5-6 membered monocyclic heteroaryl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, a 4-7 membered saturated or partially unsaturated heterocyclic ring having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur, a 7-10 membered bicyclic saturated or partially unsaturated heterocyclic ring having 1-5 heteroatoms independently selected from nitrogen, oxygen or sulfur, or an 8-10 membered bicyclic heteroaryl ring having 1-5 heteroatoms independently selected from nitrogen, oxygen, or sulfur;
- each R1, R2, and R3 is independently selected from the group consisting of hydrogen, halogen, deuterium, CF3, CN, OR, SR, NRR, NRCOR, NRCONRR, NRCO2R, COR, CO2R, NOR, NO2, CONRR, OC(O)NRR, SO2R, SO2NRR, NRSO2R, NRSO2NRR, C(O)C(O)R, or C(O)CH2C(O)R, alkyl, aryl, heteroaryl and morpholino, wherein either R1 and R2, or R2 and R3 are optionally taken together to form a 4-8 membered saturated, partially unsaturated, or fully unsaturated ring having 0-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur; and z is 0, 1 or 2;
- each R is independently selected from hydrogen or an optionally substituted C1-C4 aliphatic moiety, wherein:
- or alternately, two R moieties bound to the same nitrogen atom are optionally taken together with the nitrogen atom to form a 3-7 membered saturated, partially unsaturated, or fully unsaturated ring having 1-2 additional heteroatoms independently selected from nitrogen, oxygen, or sulfur;
- B is selected from:
- R4, R5, R6 and R7 are independently selected from a substituted or unsubstituted C1 to C12 alkyl, a substituted or unsubstituted C1 to C12 alkenyl or a substituted or unsubstituted C1 to C12 alkynyl;
- X is O, S; and
- C is a saturated or unsaturated heteroaryl or a saturated or unsaturated C1 to C7 heterocyclic containing one or more hetero atoms wherein the heteroatoms are independently selected from N, O or S;
- or C a fused ring; and
- wherein any one or more H is optionally replaced by a deuterium.
-
- (a) arresting, delaying the onset (i.e., the period prior to clinical manifestation of a disorder) and/or reducing the risk of developing or worsening a disorder;
- (b) relieving or alleviating at least one symptom of a disorder in a mammal, including for example, cancer; or
- (c) relieving or alleviating the intensity and/or duration of a manifestation of a disorder experienced by a mammal including, but not limited to, those which are in response to a given stimulus (e.g., pressure, tissue injury or cold temperature).
- Ring A is selected from the group consisting of one or more monocyclic aryl, one or more heteroaryl, a 3-7 membered saturated or partially unsaturated carbocyclic ring, an 8-10 membered bicyclic saturated, partially unsaturated or aryl ring, a 5-6 membered monocyclic heteroaryl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, a 4-7 membered saturated or partially unsaturated heterocyclic ring having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur, a 7-10 membered bicyclic saturated or partially unsaturated heterocyclic ring having 1-5 heteroatoms independently selected from nitrogen, oxygen or sulfur, or an 8-10 membered bicyclic heteroaryl ring having 1-5 heteroatoms independently selected from nitrogen, oxygen, or sulfur;
- each R1, R2, and R3 independently selected from the group consisting of hydrogen, halogen, deuterium, CF3, CN, OR, SR, NRR, NRCOR, NRCONRR, NRCO2R, COR, CO2R, NOR, NO2, CONRR, OC(O)NRR, SO2R, SO2NRR, NRSO2R, NRSO2NRR, C(O)C(O)R, or C(O)CH2C(O)R, alkyl, aryl, heteroaryl and morpholino, wherein either R1 and R2, or R2 and R3 are optionally taken together to form a 4-8 membered saturated, partially unsaturated, or fully unsaturated ring having 0-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur;
- each R is independently selected from hydrogen or an optionally substituted C1-C4 aliphatic moiety (i.e. alkyl, alkenyl, or alkynyl), wherein:
- or alternately, two R moieties bound to the same nitrogen atom are optionally taken together with the nitrogen atom to form a 3-7 membered saturated, partially unsaturated, or fully unsaturated ring having 1-2 additional heteroatoms independently selected from nitrogen, oxygen, or sulfur;
- B is selected from:
- R4, R5, R6 and R7 are independently selected from a substituted or unsubstituted C1 to C12 alkyl, a substituted or unsubstituted C1 to C12 alkenyl or a substituted or unsubstituted C1 to C12 alkynyl;
- X is O, S; and
- C is a saturated or unsaturated heteroaryl or a saturated or unsaturated C1 to C7 heterocyclic containing one or more hetero atoms wherein the heteroatoms are independently selected from N, O or S;
- or C is a fused ring; and
- wherein any one or more H is optionally replaced by a deuterium.
- wherein Y is N, O or S; and
- C is selected from:
wherein the ring is optionally substituted with one or more R10 and R11, wherein R10 and R11 are independently selected from a substituted or unsubstituted C1 to C12 alkyl, a substituted or unsubstituted C1 to C12 alkenyl or a substituted or unsubstituted C1 to C12 alkynyl, an ether, a thioether, aryl,
-
- n is 1, 2 or 3;
- X1 is O or S;
Report of Representative Compounds |
SM | Quantity | Product | Quantity | HPLC | HNMR | LCMS[M + H]+ |
SM-00 | 190 | mg | BPS- | 124 mg + 32 mg | >95% | Passed | 304 |
02084-01 | SM-00 | ||||||
SM-00 | 9.3 | mg | BPS- | 254 mg + 84 mg | >95% | Passed | 304 |
SM-00 | 13 | mg | 02084-01 | SM-00 | 304 |
SM-00 | 176 | mg | 304 | |||||
SM-00 | 190 | mg | 304 | |||||
BPS- | 56 | mg | BPS- | 7.1 | mg | 95.0% | Passed | 417 |
02084-01 | 02083-00 | |||||||
BPS- | 56 | mg | BPS- | 22 | mg | 96.1% | Passed | 375 |
02084-01 | 02084-00 | |||||||
BPS- | 96 | mg | BPS- | 30-40 | mg | >90% | Passed | |
02084-01 | 02085-01 | |||||||
BPS- | 30-40 | mg | BPS- | 0 | mg | |||
02085-01 | 02085-00 |
BPS- | 65 mg + 36 mg | BPS- | 25-30 | mg | >90% | Passed | |
02084-01 | 02086-01 |
BPS- | 25-30 | mg | BPS- | 0 | mg | |||
02086-01 | 02085-00 | |||||||
BPS- | 56 | mg | BPS- | 42 | mg | 97.1% | Passed | 332 |
02084-01 | 02087-00 | |||||||
Claims (12)
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/874,306 US8349832B2 (en) | 2009-09-02 | 2010-09-02 | Compounds and compositions for treating cancer |
PCT/US2011/025022 WO2012030408A1 (en) | 2010-09-02 | 2011-02-16 | Compounds and compositions for treating cancer |
US13/028,571 US8318737B2 (en) | 2009-09-02 | 2011-02-16 | Compounds and compositions for treating cancer |
US13/162,632 US20120157455A1 (en) | 2009-09-02 | 2011-06-17 | Compounds And Compositions For Treating Cancer |
US13/679,522 US20130203757A1 (en) | 2009-09-02 | 2012-11-16 | Compounds And Compositions For Treating Cancer |
US13/863,103 US20130237539A1 (en) | 2009-09-02 | 2013-04-15 | Compounds and Compositions for Treating Cancer |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US27575409P | 2009-09-02 | 2009-09-02 | |
US12/874,306 US8349832B2 (en) | 2009-09-02 | 2010-09-02 | Compounds and compositions for treating cancer |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US13/028,571 Continuation-In-Part US8318737B2 (en) | 2009-09-02 | 2011-02-16 | Compounds and compositions for treating cancer |
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Publication Number | Publication Date |
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US20110053938A1 US20110053938A1 (en) | 2011-03-03 |
US8349832B2 true US8349832B2 (en) | 2013-01-08 |
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WO (1) | WO2012030408A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20140024639A1 (en) * | 2012-07-20 | 2014-01-23 | The Broad Institute, Inc. | Compounds, Compositions, and Methods for Cancer Therapy |
US10766865B2 (en) | 2012-10-16 | 2020-09-08 | Sumitomo Dainippon Pharma Oncology, Inc. | PKM2 modulators and methods for their use |
US11712433B2 (en) | 2019-03-22 | 2023-08-01 | Sumitomo Pharma Oncology, Inc. | Compositions comprising PKM2 modulators and methods of treatment using the same |
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Publication number | Priority date | Publication date | Assignee | Title |
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US9801922B2 (en) | 2011-08-03 | 2017-10-31 | University Of Iowa Research Foundation | Compositions and methods of treating cancer |
WO2014032019A2 (en) * | 2012-08-23 | 2014-02-27 | Georgetown University | Compounds and methods of use thereof for treating tumors |
EP3708170A1 (en) | 2014-05-05 | 2020-09-16 | BioVentures, LLC | Compositions and methods for inhibiting antiapoptotic bcl-2 proteins as anti-aging agents |
CA2955972A1 (en) | 2014-07-22 | 2016-01-28 | Bioventures, Llc. | Compositions and methods for selectively depleting senescent cells |
EP3328372A4 (en) | 2015-07-28 | 2019-03-20 | University Of Iowa Research Foundation | Compositions and methods of treating cancer |
CA3018991A1 (en) | 2016-04-21 | 2017-10-26 | Bioventures, Llc | Compounds that induce degradation of anti-apoptotic bcl-2 family proteins and the uses thereof |
EP3474879A4 (en) | 2016-06-24 | 2020-05-06 | University of Iowa Research Foundation | Compositions and methods of treating melanoma |
WO2019075367A1 (en) | 2017-10-13 | 2019-04-18 | Tolero Pharmaceuticals, Inc. | Pkm2 activators in combination with reactive oxygen species for treatment of cancer |
WO2019221755A1 (en) * | 2018-05-18 | 2019-11-21 | Bioventures, Llc | Piperlongumine analogues and uses thereof |
US11529335B2 (en) | 2020-07-31 | 2022-12-20 | University Of Iowa Research Foundation | Compositions and methods for treating cancer |
WO2023114455A1 (en) * | 2021-12-17 | 2023-06-22 | University Of Florida Research Foundation, Incorporated | Discovery of piperlongumine as a novel e3 ligase ligand |
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